The Spy Loses a Dear Soul: Remembering Bill Rolle

This morning, I received a somewhat anticipated email informing me that Bill Rolle had comfortably passed away the night before with his family at his side. The death of a friend is always a deeply sad moment but the news of Bill’s death carried far more significance for this editor. So much so that I wanted to document as best I could the powerful impact that Bill Rolle had on me and this publication.

Bill Rolle

Like many other nonprofit leaders on the Mid-Shore looking for help, it was the MSCF’s Buck Duncan who thought Bill and I should meet in 2012. I had just started the Talbot Spy the year before and was eager to connect with a local leader in the community to help get the word out about its existence. Buck thought this highly regarded former marketing executive from Bethesda might be the kind of outreach champion we desperately needed to kick start this new form of community news.

And so we had a blind date, as Bill would label it, to proceed with a due diligence session at Bill’s official office, a.k.a. Panera Bread off of Route 50.

It was a matter of seconds for Bill to grasp the potential of a Spy in Talbot. Those decades of public relations skills, including heading up his own firm, were quickly used to assess the business model and led to an almost instantaneous friendship.

In the years ahead, Bill would be an early confidant, ambassador at large, sales director, and the Talbot Spy’s first secret agent. With over 20 years living just outside St. Michaels with his wife, Carol, Rolle had devoted his retirement to area nonprofits, mentoring them into the new brave world of marketing while also committed to their mission and funding needs. I suspect over his time in Talbot County, Bill must have served on perhaps 20 different boards, as well as kept active memberships with the Talbot Country Club, the Rotary, and countless Catholic Church-related causes.

There was never a moment in our history that he hesitated to introduce the Spy to some of the county’s most influential  business leaders and philanthropists. More importantly, to a newspaper eager to be known for its nonpartisan, education-derived mission, Bill introduced me to the Republican Party in Talbot County, and its then two dynamic leaders, Nick Panuzio and David Montgomery. That critical new connection created a long-lasting trust between the local GOP and the dozens of candidates they recruited that the Spy would give all candidates similar and fair treatment.

To Bill’s credit, and despite my best efforts to push him more to the center of things politically, he never strayed from his conservative roots. Profoundly religious and educated in the great Roman Catholic tradition at Georgetown, Bill never hesitated to mention his strong pro-life stance or his general distrust of most Democrats. And yet, for Bill, those kinds of discussions always contained great humor, gentle kidding, and respect for all different points of view. We began discussing politics at Panera Bread the first time we met and continued that debate until the Rolles left at the beginning of the Trump presidency.

But what lingers most in my memories of this special breed of gentleman was the warmth of his humor. The master of gentle trash talk, be it someone’s golf game or friendly competition with his peers to sell the most raffle tickets, a certain glow came from those Rolle barbs across the room.

Bill and I never formally said goodbye when he and Carol moved to the Western Shore. Perhaps I was avoiding acknowledging the eviviable that comes with that kind of transition. But what was important for me to tell Bill before he left town was how grateful I was for his endless cheerleading, sound advice, and, most importantly, a close friendship with this extraordinary soul. I know he left this world knowing that was the case.

Dave Wheelan is the publisher of the Spy Newspapers.